FI95697C - Laktidin valmistus dehydratoimalla sopivasti vesipitoista maitohapposyötettä - Google Patents

Laktidin valmistus dehydratoimalla sopivasti vesipitoista maitohapposyötettä Download PDF

Info

Publication number: FI95697C
Authority: FI; Finland
Prior art keywords: lactic acid; product; feed; crude; distillation
Prior art date: 1990-09-18

Application number

FI931185A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI931185A0 (fi

FI95697B (fi

FI931185L (fi

Inventor

Richard G Sinclair

Richard A Markle

Russell K Smith

Original Assignee

Biopak Technology Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1990-09-18

Filing date

1993-03-17

Publication date

1996-03-11

1993-03-17 Application filed by Biopak Technology Ltd filed Critical Biopak Technology Ltd

1993-03-17 Publication of FI931185A0 publication Critical patent/FI931185A0/fi

1993-03-17 Publication of FI931185L publication Critical patent/FI931185L/fi

1995-11-30 Application granted granted Critical

1995-11-30 Publication of FI95697B publication Critical patent/FI95697B/fi

1996-03-11 Publication of FI95697C publication Critical patent/FI95697C/fi

Links

JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 title claims abstract description 105
235000014655 lactic acid Nutrition 0.000 title claims abstract description 51
JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 title claims abstract description 49
239000004310 lactic acid Substances 0.000 title claims abstract description 48
238000002360 preparation method Methods 0.000 title claims description 11
230000018044 dehydration Effects 0.000 title description 4
238000006297 dehydration reaction Methods 0.000 title description 4
238000000034 method Methods 0.000 claims abstract description 55
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 33
238000006243 chemical reaction Methods 0.000 claims abstract description 16
238000010438 heat treatment Methods 0.000 claims abstract description 10
238000006116 polymerization reaction Methods 0.000 claims abstract description 7
239000000047 product Substances 0.000 claims description 40
238000004821 distillation Methods 0.000 claims description 36
239000012043 crude product Substances 0.000 claims description 13
239000002904 solvent Substances 0.000 claims description 12
238000004519 manufacturing process Methods 0.000 claims description 10
238000000926 separation method Methods 0.000 claims description 9
238000004448 titration Methods 0.000 claims description 8
OZZQHCBFUVFZGT-UHFFFAOYSA-N 2-(2-hydroxypropanoyloxy)propanoic acid Chemical compound CC(O)C(=O)OC(C)C(O)=O OZZQHCBFUVFZGT-UHFFFAOYSA-N 0.000 claims description 7
229920000642 polymer Polymers 0.000 claims description 6
239000011230 binding agent Substances 0.000 claims description 2
238000004508 fractional distillation Methods 0.000 claims description 2
239000012528 membrane Substances 0.000 claims description 2
238000001953 recrystallisation Methods 0.000 claims description 2
238000000605 extraction Methods 0.000 claims 2
238000005194 fractionation Methods 0.000 claims 2
YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims 1
239000013078 crystal Substances 0.000 claims 1
238000002425 crystallisation Methods 0.000 claims 1
230000008025 crystallization Effects 0.000 claims 1
150000003903 lactic acid esters Chemical class 0.000 claims 1
230000003204 osmotic effect Effects 0.000 claims 1
239000000376 reactant Substances 0.000 claims 1
239000012429 reaction media Substances 0.000 claims 1
238000003809 water extraction Methods 0.000 claims 1
JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 abstract description 18
239000000203 mixture Substances 0.000 abstract description 9
JJTUDXZGHPGLLC-IMJSIDKUSA-N 4511-42-6 Chemical compound C[C@@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-IMJSIDKUSA-N 0.000 abstract description 7
125000004122 cyclic group Chemical class 0.000 abstract description 2
230000003190 augmentative effect Effects 0.000 abstract 1
150000004996 alkyl benzenes Chemical class 0.000 description 14
239000003054 catalyst Substances 0.000 description 12
238000004817 gas chromatography Methods 0.000 description 12
238000004064 recycling Methods 0.000 description 11
-1 lactoyl Chemical group 0.000 description 9
239000000463 material Substances 0.000 description 6
239000007858 starting material Substances 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
230000007246 mechanism Effects 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
229910014033 C-OH Inorganic materials 0.000 description 4
229910014570 C—OH Inorganic materials 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000006798 ring closing metathesis reaction Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
238000005406 washing Methods 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 3
229940061720 alpha hydroxy acid Drugs 0.000 description 3
150000001280 alpha hydroxy acids Chemical class 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
239000004721 Polyphenylene oxide Substances 0.000 description 2
229920006362 Teflon® Polymers 0.000 description 2
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
239000006184 cosolvent Substances 0.000 description 2
KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
239000012634 fragment Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
230000011987 methylation Effects 0.000 description 2
238000007069 methylation reaction Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
229920000570 polyether Polymers 0.000 description 2
238000000746 purification Methods 0.000 description 2
IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 2
MCVUKOYZUCWLQQ-UHFFFAOYSA-N tridecylbenzene Chemical compound CCCCCCCCCCCCCC1=CC=CC=C1 MCVUKOYZUCWLQQ-UHFFFAOYSA-N 0.000 description 2
239000002699 waste material Substances 0.000 description 2
JJTUDXZGHPGLLC-ZXZARUISSA-N (3r,6s)-3,6-dimethyl-1,4-dioxane-2,5-dione Chemical compound C[C@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-ZXZARUISSA-N 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
VPVXHAANQNHFSF-UHFFFAOYSA-N 1,4-dioxan-2-one Chemical compound O=C1COCCO1 VPVXHAANQNHFSF-UHFFFAOYSA-N 0.000 description 1
MNKRTDOUBUSQHX-UHFFFAOYSA-N 2,4-dihydroxy-2-methyl-3-oxopentanoic acid Chemical compound CC(O)C(=O)C(C)(O)C(O)=O MNKRTDOUBUSQHX-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
241001649081 Dina Species 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000010908 decantation Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
229920006237 degradable polymer Polymers 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
238000012691 depolymerization reaction Methods 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000004907 flux Effects 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
125000005474 octanoate group Chemical group 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000002572 peristaltic effect Effects 0.000 description 1
239000012466 permeate Substances 0.000 description 1
238000005086 pumping Methods 0.000 description 1
238000010926 purge Methods 0.000 description 1
238000002390 rotary evaporation Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
241000894007 species Species 0.000 description 1
239000012974 tin catalyst Substances 0.000 description 1
150000003606 tin compounds Chemical class 0.000 description 1
KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
239000013638 trimer Substances 0.000 description 1
238000010977 unit operation Methods 0.000 description 1
239000011800 void material Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/12—1,4-Dioxanes; Hydrogenated 1,4-dioxanes not condensed with other rings
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/19—Details relating to the geometry of the reactor
- B01J2219/194—Details relating to the geometry of the reactor round
- B01J2219/1941—Details relating to the geometry of the reactor round circular or disk-shaped
- B01J2219/1942—Details relating to the geometry of the reactor round circular or disk-shaped spherical
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
- C08J2367/04—Polyesters derived from hydroxy carboxylic acids, e.g. lactones

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Manufacturing & Machinery (AREA)
Materials Engineering (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Wood Science & Technology (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Polyesters Or Polycarbonates (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Fodder In General (AREA)
Saccharide Compounds (AREA)
Medicinal Preparation (AREA)
Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Freezing, Cooling And Drying Of Foods (AREA)

FI931185A 1990-09-18 1993-03-17 Laktidin valmistus dehydratoimalla sopivasti vesipitoista maitohapposyötettä FI95697C (fi)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US58412690		1990-09-18
US07/584,126 US5274127A (en)	1990-09-18	1990-09-18	Lactide production from dehydration of aqueous lactic acid feed
PCT/US1991/006774 WO1992005167A1 (en)	1990-09-18	1991-09-18	Lactide production from dehydration of aqueous lactic acid feed
US9106774		1991-09-18

Publications (4)

Publication Number	Publication Date
FI931185A0 FI931185A0 (fi)	1993-03-17
FI931185L FI931185L (fi)	1993-03-17
FI95697B FI95697B (fi)	1995-11-30
FI95697C true FI95697C (fi)	1996-03-11

Family

ID=24336030

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI931185A FI95697C (fi)	1990-09-18	1993-03-17	Laktidin valmistus dehydratoimalla sopivasti vesipitoista maitohapposyötettä

Country Status (22)

Country	Link
US (1)	US5274127A (de)
EP (1)	EP0552226B1 (de)
JP (1)	JPH06504762A (de)
KR (1)	KR0171432B1 (de)
CN (1)	CN1061222A (de)
AT (1)	ATE109141T1 (de)
AU (1)	AU653179B2 (de)
BR (1)	BR9106855A (de)
CA (1)	CA2091691A1 (de)
DE (1)	DE69103159T2 (de)
DK (1)	DK0552226T3 (de)
ES (1)	ES2057917T3 (de)
FI (1)	FI95697C (de)
HK (1)	HK175595A (de)
IE (1)	IE62721B1 (de)
IL (1)	IL99519A0 (de)
MX (1)	MX9101131A (de)
MY (1)	MY107225A (de)
NZ (1)	NZ239824A (de)
PT (1)	PT98998A (de)
WO (1)	WO1992005167A1 (de)
ZA (1)	ZA917410B (de)

Families Citing this family (36)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5319107A (en) *	1990-09-18	1994-06-07	Biopak Technology, Ltd.	Method to produce cyclic esters
US5444113A (en) *	1988-08-08	1995-08-22	Ecopol, Llc	End use applications of biodegradable polymers
US5767222A (en) *	1988-08-08	1998-06-16	Chronopol, Inc.	Degradable polydioxaneone-based materials
US5332839A (en) *	1990-09-18	1994-07-26	Biopak Technology, Ltd.	Catalytic production of lactide directly from lactic acid
US5326887A (en) *	1991-02-27	1994-07-05	E. I. Du Pont De Nemours And Company	Process for the preparation of 1,4-dioxane-2,5-diones
US5247058A (en) *	1992-01-24	1993-09-21	Cargill, Incorporated	Continuous process for manufacture of lactide polymers with controlled optical purity
US6326458B1 (en)	1992-01-24	2001-12-04	Cargill, Inc.	Continuous process for the manufacture of lactide and lactide polymers
US6005067A (en) *	1992-01-24	1999-12-21	Cargill Incorporated	Continuous process for manufacture of lactide polymers with controlled optical purity
US5247059A (en) *	1992-01-24	1993-09-21	Cargill, Incorporated	Continuous process for the manufacture of a purified lactide from esters of lactic acid
US5142023A (en) *	1992-01-24	1992-08-25	Cargill, Incorporated	Continuous process for manufacture of lactide polymers with controlled optical purity
US5258488A (en) *	1992-01-24	1993-11-02	Cargill, Incorporated	Continuous process for manufacture of lactide polymers with controlled optical purity
US5420304A (en) *	1992-03-19	1995-05-30	Biopak Technology, Ltd.	Method to produce cyclic esters
US5686630A (en) *	1993-09-29	1997-11-11	Chronopol, Inc.	Purifying cyclic esters by aqueous solvent extraction
DE69322155T2 (de) *	1992-10-02	1999-08-19	Cargill	Papier mit einer beschichtung aus schmelzstabilem polymer und dessen verfahren zur herstellung
CA2124842C (en)	1992-10-02	2003-07-15	Patrick R. Gruber	A melt-stable lactide polymer fabric and process for manufacture thereof
US5338822A (en) *	1992-10-02	1994-08-16	Cargill, Incorporated	Melt-stable lactide polymer composition and process for manufacture thereof
US6005068A (en) *	1992-10-02	1999-12-21	Cargill Incorporated	Melt-stable amorphous lactide polymer film and process for manufacture thereof
JPH07165753A (ja) *	1993-12-08	1995-06-27	Musashino Kagaku Kenkyusho:Kk	ラクチドの精製方法
JPH10109983A (ja) *	1996-10-04	1998-04-28	Mitsubishi Gas Chem Co Inc	環状エステルの製造方法および精製方法
US6326042B1 (en)	1997-05-29	2001-12-04	The Curators Of The University Of Missouri	Antimicrobial use of heat-treated lactic and/or glycolic acid compositions for treatment of ground meats
US5900266A (en) *	1997-05-29	1999-05-04	The Curators Of The University Of Missouri	Heat-treated lactic and/or glycolic acid compositions and methods of use
US6313319B1 (en)	1998-09-25	2001-11-06	Shimadzu Corporation	Method for purifying lactide and lactide for food additives
AU2098901A (en)	1999-12-13	2001-06-18	Michigan State University	Process for the preparation of polymers of dimeric cyclic esters
CN100545159C (zh) *	2005-12-19	2009-09-30	奇美实业股份有限公司	α-羟基有机酸环酯类化合物的制造方法
US7723461B1 (en)	2005-12-22	2010-05-25	Tetramer Technologies, Llc	Polymeric materials from renewable resources
BRPI0809330B8 (pt) *	2007-03-30	2021-05-25	Laccure Ab	uso de um ou mais oligômeros de ácido láctico, e, composição farmacêutica
EP2072508A1 (de)	2007-12-19	2009-06-24	Galactic S.A.	Herstellungsverfahren von Laktid
CN101434594B (zh) *	2008-12-19	2012-05-02	河北科技大学	混合溶剂法制备丙交酯的方法
KR101154029B1 (ko)	2009-05-20	2012-06-07	한국화학연구원	젖산에스테르로부터 락타이드의 직접 전환용 촉매 및 이를 이용한 락타이드의 제조방법
US8383851B2 (en) *	2010-09-15	2013-02-26	Caravan Ingredients Inc.	Lactylate synthesis methods using dilactides
EP2633028B1 (de)	2010-10-28	2014-04-30	Total Marketing Services	Verwendung von monascus in der herstellung von organischen säuren
KR20140053129A (ko) *	2011-07-15	2014-05-07	플라시카 리미티드	분리방법
WO2013160485A1 (de)	2012-04-28	2013-10-31	Uhde Inventa-Fischer Gmbh	Verfahren zur kontinuierlichen herstellung von lactid direkt aus konzentrierter milchsäure
KR101428340B1 (ko)	2012-12-31	2014-08-07	현대자동차주식회사	이온성 용매를 이용한 락타이드 제조법
KR101704563B1 (ko)	2015-10-12	2017-02-08	한국화학연구원	락타이드 정제공정을 이용한 락타이드 제조방법 및 제조장치
CN107118200B (zh)	2016-02-24	2020-02-28	香港纺织及成衣研发中心有限公司	一种利用乳酸催化合成丙交酯的方法

Family Cites Families (41)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA863673A (en) *		1971-02-16	K. Schneider Allan	Absorbable suture
DE221786C (de) *
DE53074C (de) *			Frau A. LA GUAYRA MAYO in Great Falls, Cty Cascade, und W. HUDNALL in Helena, Cty Lewisand Clark, V. St. A	Verstellbare Säumvorrichtung für Nähmaschinen
DE267826C (de) *	1912-12-28	1913-12-02	Chemische Werke	Verfahren zur Darstellung von lactid
US1095205A (en) *	1913-05-15	1914-05-05	Chemische Werke Vorm Dr Heinrich Byk	Manufacture of lactid.
US1594843A (en) *	1921-08-19	1926-08-03	Du Pont	Purification of lactic acid
US1995970A (en) *	1931-04-04	1935-03-26	Du Pont	Polymeric lactide resin
US2163268A (en) *	1933-12-12	1939-06-20	Du Pont	Method for making cyclic esters
US2174491A (en) *	1938-06-28	1939-09-26	Paul D Watson	Method of making lactic acid resinous products
US2189572A (en) *	1938-09-01	1940-02-06	Paul D Watson	Process for fractionating resinous products
US2703316A (en) *	1951-06-05	1955-03-01	Du Pont	Polymers of high melting lactide
US2668162A (en) *	1952-03-20	1954-02-02	Du Pont	Preparation of high molecular weight polyhydroxyacetic ester
US2758987A (en) *	1952-06-05	1956-08-14	Du Pont	Optically active homopolymers containing but one antipodal species of an alpha-monohydroxy monocarboxylic acid
US2768973A (en) *	1954-11-30	1956-10-30	Du Pont	Preparation of glycolaldehyde by hydrolysis of 4-chloro-2-oxodioxolane
US3322791A (en) *	1963-09-26	1967-05-30	Ethicon Inc	Preparation of optically active lactides
DE1194142B (de) *	1963-11-19	1965-06-03	Bayer Ag	Verfahren zum UV-Stabilisieren von Polycarbonaten
BE674355A (de) *	1964-12-28	1966-06-27
US3457280A (en) *	1967-06-12	1969-07-22	American Cyanamid Co	Alpha-glycolide and methods for the isolation thereof
US3435008A (en) *	1967-08-22	1969-03-25	American Cyanamid Co	Method for preparation of isomerically pure beta-glycolide and polymerization method for glycolide compositions employing partial hydrolyzate of said beta-glycolide
US3597450A (en) *	1969-11-05	1971-08-03	American Cyanamid Co	Preparation of glycolide polymerizable into polyglycolic acid of consistently high molecular weight
US3867190A (en) *	1971-10-18	1975-02-18	American Cyanamid Co	Reducing capillarity of polyglycolic acid sutures
US3736646A (en) *	1971-10-18	1973-06-05	American Cyanamid Co	Method of attaching surgical needles to multifilament polyglycolic acid absorbable sutures
US3960152A (en) *	1974-01-21	1976-06-01	American Cyanamid Company	Surgical sutures of unsymmetrically substituted 1,4-dioxane-2,5-diones
US4033938A (en) *	1974-01-21	1977-07-05	American Cyanamid Company	Polymers of unsymmetrically substituted 1,4-dioxane-2,5-diones
DE3632103A1 (de) *	1986-09-20	1988-03-24	Boehringer Ingelheim Kg	Verfahren zur herstellung von lactid
EP0261572A1 (de) *	1986-09-20	1988-03-30	Boehringer Ingelheim Kg	Verfahren zur Herstellung von Lactid
DE3708915C2 (de) *	1987-03-19	1996-04-04	Boehringer Ingelheim Kg	Verfahren zur Herstellung von Lactid
DE3778111D1 (de) *	1986-10-24	1992-05-14	Boehringer Ingelheim Kg	Verfahren zur herstellung und reinigung thermolabiler verbindungen.
DE3781133T2 (de) *	1986-12-19	1993-06-24	Akzo Nv	Herstellung von polymilchsaeure und copolymeren daraus.
US4835293A (en) *	1987-02-24	1989-05-30	E. I. Du Pont De Nemours And Company	Atmospheric pressure process for preparing pure cyclic esters
NL8702563A (nl) *	1987-10-28	1989-05-16	Cca Biochem B V	Polymeer lactide, werkwijze voor het bereiden van een dergelijk polymeer lactide, alsmede een samenstelling, die een dergelijk polymeer lactide bevat.
US5068418A (en) *	1989-05-08	1991-11-26	Uop	Separation of lactic acid from fermentation broth with an anionic polymeric absorbent
US5075115A (en) *	1990-04-02	1991-12-24	Fmc Corporation	Process for polymerizing poly(lactic acid)
US5091544A (en) *	1990-05-08	1992-02-25	E. I. Du Pont De Nemours And Company	Process for rapid conversion of oligomers to cyclic esters
US5023349A (en) *	1990-05-08	1991-06-11	E. I. Du Pont De Nemours And Company	Continuous process for rapid conversion of oligomers to cyclic esters
US5043458A (en) *	1990-05-03	1991-08-27	E. I. Du Pont De Nemours And Company	One-step continuous process for preparing cyclic esters
EP0531458B1 (de) *	1990-05-03	1997-08-13	E.I. Du Pont De Nemours And Company	Verfahren zur schnellen herstellung cyclischer ester
US5023350A (en) *	1990-05-24	1991-06-11	E. I. Du Pont De Nemours And Company	Process for the purification of cyclic esters
US5138074A (en) *	1990-06-28	1992-08-11	E. I. Du Pont De Nemours And Company	Continuous catalyzed vapor phase dimeric cyclic ester process
US5332839A (en) *	1990-09-18	1994-07-26	Biopak Technology, Ltd.	Catalytic production of lactide directly from lactic acid
US5089632A (en) *	1991-01-30	1992-02-18	E. I. Du Pont De Nemours And Company	Process for preparing cyclic esters using a fluorocarbon

1990
- 1990-09-18 US US07/584,126 patent/US5274127A/en not_active Expired - Fee Related
1991
- 1991-09-17 ZA ZA917410A patent/ZA917410B/xx unknown
- 1991-09-17 IE IE327291A patent/IE62721B1/en not_active IP Right Cessation
- 1991-09-17 NZ NZ239824A patent/NZ239824A/xx unknown
- 1991-09-18 MY MYPI91001692A patent/MY107225A/en unknown
- 1991-09-18 ES ES91917931T patent/ES2057917T3/es not_active Expired - Lifetime
- 1991-09-18 MX MX9101131A patent/MX9101131A/es not_active IP Right Cessation
- 1991-09-18 AT AT91917931T patent/ATE109141T1/de not_active IP Right Cessation
- 1991-09-18 PT PT98998A patent/PT98998A/pt not_active Application Discontinuation
- 1991-09-18 DE DE69103159T patent/DE69103159T2/de not_active Expired - Fee Related
- 1991-09-18 EP EP91917931A patent/EP0552226B1/de not_active Expired - Lifetime
- 1991-09-18 JP JP3516738A patent/JPH06504762A/ja active Pending
- 1991-09-18 WO PCT/US1991/006774 patent/WO1992005167A1/en not_active Ceased
- 1991-09-18 KR KR1019930700809A patent/KR0171432B1/ko not_active Expired - Fee Related
- 1991-09-18 AU AU87292/91A patent/AU653179B2/en not_active Ceased
- 1991-09-18 DK DK91917931.7T patent/DK0552226T3/da active
- 1991-09-18 CN CN91108029A patent/CN1061222A/zh active Pending
- 1991-09-18 BR BR919106855A patent/BR9106855A/pt not_active Application Discontinuation
- 1991-09-18 CA CA002091691A patent/CA2091691A1/en not_active Abandoned
- 1991-09-19 IL IL99519A patent/IL99519A0/xx unknown
1993
- 1993-03-17 FI FI931185A patent/FI95697C/fi not_active IP Right Cessation
1995
- 1995-11-16 HK HK175595A patent/HK175595A/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
MX9101131A (es)	1992-05-04
US5274127A (en)	1993-12-28
NZ239824A (en)	1993-01-27
KR0171432B1 (ko)	1999-02-01
HK175595A (en)	1995-11-24
EP0552226B1 (de)	1994-07-27
JPH06504762A (ja)	1994-06-02
IE913272A1 (en)	1992-02-25
DE69103159D1 (de)	1994-09-01
AU8729291A (en)	1992-04-15
DE69103159T2 (de)	1994-11-03
ES2057917T3 (es)	1994-10-16
IL99519A0 (en)	1992-08-18
WO1992005167A1 (en)	1992-04-02
PT98998A (pt)	1992-07-31
MY107225A (en)	1995-10-31
FI931185A0 (fi)	1993-03-17
DK0552226T3 (da)	1994-09-12
ATE109141T1 (de)	1994-08-15
FI95697B (fi)	1995-11-30
ZA917410B (en)	1992-05-27
BR9106855A (pt)	1993-08-24
CN1061222A (zh)	1992-05-20
KR930702331A (ko)	1993-09-08
FI931185L (fi)	1993-03-17
IE62721B1 (en)	1995-02-22
EP0552226A1 (de)	1993-07-28
CA2091691A1 (en)	1992-03-19
AU653179B2 (en)	1994-09-22

Legal Events

Date	Code	Title	Description
1995-11-01	BB	Publication of examined application
1997-09-18	MM	Patent lapsed

Publication	Publication Date	Title
AU653179B2 (en)	1994-09-22	Lactide production from dehydration of aqueous lactic acid feed
JP2922303B2 (ja)	1999-07-19	ヒドロキシ酸及びその誘導体からの環状エステルの製造方法
EP0722433B1 (de)	2000-01-26	Verfahren zur herstellung von cyclischen estern
JP3236289B2 (ja)	2001-12-10	触媒を用いた乳酸からラクチドを直接製造する方法
US5502215A (en)	1996-03-26	Method for purification of lactide
JP5679411B2 (ja)	2015-03-04	ポリ乳酸の製造方法
EP2980084B1 (de)	2018-12-05	Verfahren zur herstellung von glycolid
CN1501923A (zh)	2004-06-02	乙交酯生产方法以及用于生产乙交酯的乙醇酸低聚物
KR101809663B1 (ko)	2017-12-15	알킬 프로피오네이트와 물 혼합용매를 이용한 광학순도가 향상된 락타이드의 제조방법
Upare et al.	2019	Integrated production of polymer-grade lactide from aqueous lactic acid by combination of heterogeneous catalysis and solvent crystallization with ethanol
KR20080018650A (ko)	2008-02-28	광학적으로 순수한 락티드의 분리방법
US9988488B2 (en)	2018-06-05	Catalyst for poly(lactide) synthesis and uses thereof
CA2132843C (en)	2006-08-01	Process for the production of cyclic esters from hydroxy acids and derivatives therefrom
RU2576038C1 (ru)	2016-02-27	Способ получения гликолида
JP4002083B2 (ja)	2007-10-31	テレフタル酸ジメチル組成物及びその製造方法
JPH1036366A (ja)	1998-02-10	ラクチドの製造方法